I'm just going to come right out and say it: Entrepreneurs are terrible at taking vacations. We go for years at a time without taking them, and when we do take one, most of us spend a majority of our time working from our laptops instead of actually enjoying ourselves.

And I get it--I was once in the same boat.

What even is a "working" vacation?

In my experience, entrepreneurs tend to take two types of vacations. They take either a "working vacation," during which they end up working the entire time (which isn't really a vacation) or an off-grid vacation with no internet, no computer, and no phone.

I used to be the "working vacation" kind of guy. But when planning my last vacation--a three week trip to Italy--I thought about how I could take a vacation that blends the line between a working vacation and an off-grid vacation. I'm not quite ready to take an off-grid vacation (and quite frankly, I don't think I'd really enjoy that), but I didn't want to get bogged down in actual work.

The result was the best vacation I've ever had. I was able to actually take time off without worrying about my business, and I wasn't hit with an avalanche of work when I came back. I think this could be the new "working vacation" for entrepreneurs, which allows you to stay in the loop and keep your business moving forward but still spend the vast majority of your vacation relaxing and being present.

Here's how I did it.

Zoom will ruin your vacation

As the founder and CEO of a fully remote business, I spend a lot of my time in Zoom meetings. So the first thing I did when planning my vacation was to cancel all Zoom meetings for the time I was away. I told my team that I would be available asynchronously via email, Asana, and Slack, but I would not be attending any live meetings whatsoever.

The problem with Zoom is that it's synchronous. Unlike asynchronous communication like email, Asana, or Slack, you have to be at your computer at a certain time and date for a Zoom meeting. That's not very conducive to a vacation, as you then have to plan your days around meetings (which inevitably create more work and more meetings).

If you want to take a vacation and actually enjoy yourself, you can't allow yourself to step into a Zoom meeting. Period.

Setting your team up for success

As a business owner, you need to have some level of trust that your team is going to do the right things while you're gone.

Before going on a vacation, it's important to set your team up for success so they can make decisions and move projects forward without your involvement. At my company, Leverage, we use my CPR Business Efficiency Framework, which helps with this. CPR stands for communicate, plan, and resource--the three areas every company needs to master to operate efficiently.

But here's how it works with regards to taking time off as a founder:

  • Communication needs to be optimized and organized, so that you can poke your head into Slack or email and quickly get the information you need from your team or review past communications as needed.

  • Planning is crucial, and not just while you're on vacation. With the right planning and project management process in place, your team will be clear on what projects they should be working on at any given moment, and you'll be able to monitor their progress from afar without micromanaging.

  • Resource involves knowledge and process documentation. With this documentation in place, your team will always be able to find the information they need to get work done, and you can rest easy knowing that all of the core processes in your business are being completed on time, by the right people, and in the right ways.

With the right operational framework in place, your team will be able to keep the business moving forward with or without your involvement. And, best of all, you can quickly check in to see how things are going without getting bogged down in meetings or having to sort through hundreds of emails and past communications.

Inbox zero is your one (and only) job

So, what's left for you to do during your vacation? Besides enjoying yourself, all you really have to do is get to inbox zero once or twice per day. I've spoken previously about the merits of inbox zero and how to achieve it, but in this case, you'll want to take it one step further by getting to inbox zero in email, your chosen internal communication tool (like Slack or Microsoft Teams), and your project management software.

Doing this will alleviate any bottlenecks for your team, and allow you to stay up to date or catch opportunities that others may have missed. Removing bottlenecks is crucial--you need to be able to give your team feedback and approvals so they can move forward with their work. With this process, you'll still be "running" your business, but you need to commit only a few hours per day and you're free to choose when those few hours take place. That means you're still in complete control of your vacation.

And the best part? Now you can actually relax without worrying about what's going on in your business or anticipating the mountain of work sitting on your desk when you return.